Iridium(III)-Catalyzed C−H Functionalization of Triarylphosphine Oxides with Diazo Dicarbonyl Compounds: Synthesis of α-Aryl 1,3-Dicarbonyl Derivatives

Abstract

A novel (pentamethylcyclopenta-1,3-dienyl)iridium(III)-catalyzed direct C–H functionalization of triarylphosphine oxides with diazo dicarbonyl compounds through carbene insertion has been developed. This strategy provides a simple and efficient route to the construction of α-arylated 1,3-dicarbonyl compounds, which are important building blocks in pharmaceutical chemistry.

Key words

triarylphosphine oxides - iridium catalysis - C–H bond activation - aryl dicarbonyl compounds

Publication History

Received: 28 January 2021

Accepted after revision: 05 March 2021

Accepted Manuscript online:
05 March 2021

Article published online:
01 April 2021

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• 12 2-[2-(Diphenylphosphoryl)phenyl]-4,4-dimethyl-1-phenylpentane-1,3-dione (3): Typical ProcedureUnder an Ar atmosphere, Ph₃P=O (1; 0.4 mmol, 2.0 equiv), [Cp*IrCl₂]₂ (2.0 mg, 1.25 mol%), AgOTf (2.6 mg, 10 mol%), and pivalic acid (10.2 mg, 0.1 mmol, 0.5 equiv) were added to an oven-dried reaction tube containing a magnetic stirrer bar. The tube was sealed, DCE (0.3 mL) was added from a syringe, and the mixture was stirred at 50 °C (oil bath) for 20 min. A solution of the diazo 1,3-dicarbonyl compound 2a (0.2 mmol, 1.0 equiv) in DCE (1.0 mL) was then added over 4 h by using a peristaltic pump. The mixture was stirred for a further 12 h then cooled to r.t. The solvent was removed in vacuo, and the residue was purified by chromatography [silica gel, PE–EtOAc (3:1)] to give a white solid; yield: 86.4 mg (90%).¹H NMR (400 MHz, CDCl₃): δ = 8.12 (m, 3 H), 7.58–7.36 (m, 11 H), 7.31 (m, 4 H), 7.24–7.18 (m, 1 H), 7.05 (dd, J = 14.4, 7.4 Hz, 1 H), 1.03 (s, 9 H). ¹³C NMR (101 MHz, CDCl₃): δ = 209.8, 195.0, 135.9, 134.2 (d, J = 13.1 Hz), 133.1, 132.7 (d, J = 9.7 Hz), 132.3, 132.2 (d, J = 2.8 Hz), 132.2, 132.1, 131.9 (d, J = 2.5 Hz), 131.8, 129.3, 128.9 (d, J = 100.8 Hz), 128.6 (dd, J = 13.6, 12.2 Hz), 128.4, 126.9 (d, J = 12.8 Hz), 58.8 (d, J = 3.6 Hz), 45.6, 27.0. ³¹P NMR (162 MHz, CDCl₃): δ = 34.3. HRMS (ESI): m/z [M + Na]⁺ calcd for C₃₁H₂₉NaO₃P: 503.1747; found: 503.1747.
• 13 CCDC 20127547 contains the supplementary crystallographic data for compound 3. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
• 14 For details, see the Supporting Information.
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